Question: Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty socks. This compound can be resolved into enantiomers and

Compound A, C8H11NO, smells as if it might have been isolated from an extract of dirty socks. This compound can be resolved into enantiomers and it dissolves in 5% aqueous HCl. Oxidation of A with concentrated HNO3, and heat gives nicotinic acid (3-pyridinecarboxylic acid; see Eq. 25.26.) When A reacts with CrO3, in pyridine, compound B (C8H9NO) is obtained. Compound B, when treated with dilute NaOD in D2O, incorporates five deuterium atoms per molecule. Identify A, and explain your reasoning.

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